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I think the silicone sealant is a good idea to hold your plug in place and keep it water tight, but I think the silicone is too soft to hold up long in Wisconsin winter driving (sand/salt being thrown around at highway speeds).
I would suggest you visit a body shop and ask them what kind of material you can apply in the wheel well (assuming this is the area you put the plug into) to coat over the silicone/plug patch area to give the outside surface some better durability. It may be tough to get something hard to stick to soft silicone, but I think the body shop would have a good recommendation for you.
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